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Triethylamine → 6-Bromo-2-(1-(difluoromethyl)-1H-pyrazol-4-yl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridine

HRID 2205946
Notes
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Reaction equation

HRID 2205946 reaction equation
[F:1][CH:2]([F:10])[N:3]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[N:4]1.[Br:11][C:12]1[CH:17]=[C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:15](I)=[CH:14][N:13]=1.C(N(CC)CC)C>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:11][C:12]1[N:13]=[CH:14][C:15]2[CH:9]=[C:8]([C:6]3[CH:5]=[N:4][N:3]([CH:2]([F:10])[F:1])[CH:7]=3)[N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:16]=2[CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 86706267N-(2-Bromo-5-iodopyridin-4-yl)methanesulfonamideHCID 867063321-(difluoromethyl)-4-ethynyl-1H-pyrazole

Product 1

HCID 867063336-Bromo-2-(1-(difluoromethyl)-1H-pyrazol-4-yl)-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridineYield 34.3%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(Difluoromethyl)-4-ethynyl-1H-pyrazole (Preparation 152, 187 mg 1.31 mmole) was dissolved in DMF (4.2 mL) and N-(2-bromo-5-iodopyridin-4-yl)methanesulfonamide (Preparation 8, 444 mg 1.17 mmole) was added. To the solution was added triethylamine (0.80 mL, 576 mg 5.7 mmole) and copper(I) iodide (9 mg 0.047 mmole). The reaction was sealed and flushed with nitrogen. Bis(triphenylphosphine)palladium dichloride (37.6 mg 0.046 mmole) was added and the reaction was again flushed with nitrogen, then heated at 60° C. for 140 minutes. The reaction was added to ethyl acetate (45 mL) and washed with water (3×15 mL) and with brine, then dried and concentrated in vacuo. The residue was purified using preparative TLC eluting with 5% ethyl acetate in chloroform to afford the title compound 157 mg. 1H-NMR (d6-acetone, 500 MHz): δ 3.37 (s, 3H), 7.06 (d, J=0.63 Hz, 1H), 7.70 (t, J=59.6 Hz, 1H), 8.04 (s, 1H), 8.16 (m, 1H), 8.51 (s, 1H), 8.73 (d, J=0.95 Hz, 1H).

Workup

  1. customThe reaction was sealed
  2. customflushed with nitrogen
  3. customthe reaction was again flushed with nitrogen
  4. additionThe reaction was added to ethyl acetate (45 mL)
  5. washwashed with water (3×15 mL) and with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified
  9. washeluting with 5% ethyl acetate in chloroform

Sources & evidence

ORD record
ord-1fb598f8bdb84792a872bcdde4e499ac
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371319B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes