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Potassium Phosphate, Tribasic → 7-(3-Methoxyphenyl)-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1615464
Notes
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Reaction equation

HRID 1615464 reaction equation
Br[C:2]1[N:10]2[C:5]([C:6]([NH2:11])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][O:21][C:22]1[CH:27]=[C:26]([C:2]2[N:10]3[C:5]([C:6]([NH2:11])=[N:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[CH2:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:25]=[CH:24][CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734370(3-Methoxyphenyl)boronic acidHCID 666123207-Bromo-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 666020177-(3-Methoxyphenyl)-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 66.4%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound (135 mg, 0.42 mmol) prepared in Example 13, 3-methoxyphenylboronic acid (96 mg, 0.63 mmol), potassium phosphate (2N, 1 mL 2.0 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (11 mg, 0.01 mmol) in dioxane (3 mL) was deoxygenated by nitrogen gas for 5 minutes, and the reactor was sealed, heated at 90° C. for 20 hours. The mixture was concentrated, extracted with DCM and sodium hydroxide (1N). The organic layer was dried, concentrated, and the crude product was purified by prep TLC using 9% methanol in DCM (with 1% ammonium hydroxide) to obtain the title compound (98 mg) having the following physical data.

Workup

  1. customthe reactor was sealed
  2. concentrationThe mixture was concentrated
  3. extractionextracted with DCM and sodium hydroxide (1N)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe crude product was purified by prep TLC

Sources & evidence

ORD record
ord-de08011049c3422f8b6b275a2afab7f0
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765754B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes