Lawesson's reagent → HCID 44554281, compound

HRID 40727Notes

Reaction equation

HRID 40727 reaction equation
F[C:2]1[C:7]([NH:8][C:9]([C:11]2[CH:12]=[C:13]3[CH:19]=[CH:18][N:17]([CH3:20])[C:14]3=[N:15][CH:16]=2)=O)=[CH:6][CH:5]=[C:4]([F:21])[N:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C=CC=CC=1>[F:21][C:4]1[N:3]=[C:2]2[S:31][C:9]([C:11]3[CH:12]=[C:13]4[CH:19]=[CH:18][N:17]([CH3:20])[C:14]4=[N:15][CH:16]=3)=[N:8][C:7]2=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 584122581-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (2,6-difluoro-pyridin-3-yl)-amide

Product 1

HCID 44554281HCID 44554281, compoundYield 167.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (2,6-difluoro-pyridin-3-yl)-amide (300 mg, 1.04 mmol) in toluene in a sealable vial was added Lawesson's Reagent (210 mg, 0.52 mmol). The vial was capped and heated to 130° C. for 12 h, cooled to room temp, and loaded directly onto a silica gel column and purified by flash column chromatography (0 to 100% EtOAc in hexanes) to afford 5-fluoro-2-(1-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-thiazolo[5,4-b]pyridine (247 mg, 83% yield). ES MS (M+H+)=285; 1H NMR δ (ppm)(DMSO-d6): 8.99 (1H, d, J=2.23 Hz), 8.64 (1H, s), 8.66-8.53 (1H, m), 7.67 (1H, d, J=3.50 Hz), 7.38 (1H, dd, J=8.74, 1.80 Hz), 6.65 (1H, d, J=3.49 Hz), 3.87 (3H, s).

Workup

  1. customThe vial was capped
  2. temperaturecooled to room temp
  3. custompurified by flash column chromatography (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-67c429421d174e2f9a8698bde6e6b997
Source dataset
uspto-grants-2013_09
Patent number
US08530483B2

Reaction notes

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