Dimethylformamide → N-Benzyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

HRID 562852Notes

Reaction equation

HRID 562852 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]([OH:12])=O)[CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.O1CCCC1.CN(C)C=O.C(Cl)Cl>O>[CH2:13]([NH:20][C:10]([C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 7

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733179PyBroPHCID 219070181H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 57595724N-Benzyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamideYield 27.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a Round bottom flask was added compound 15 (35.0 mg, 0.000216 mol) and benzylamine (0.05 mL, 0.0004 mol) and PyBroP (Bromotri(pyrrolidino)phosphonium hexafluorophosphate, 200.0 mg, 0.0004318 mol) and triethylamine (0.093 mL, 0.00067 mol) and tetrahydrofuran (5.0 mL, 0.062 mol) and N,N-dimethylformamide (10.0 mL, 0.129 mol) and methylene chloride (5.0 mL, 0.078 mol) under an atmosphere of Nitrogen. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with biotage to give product 19 (15 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with biotage

Sources & evidence

ORD record
ord-385c830e1ae54c01adb840f665070309
Source dataset
uspto-grants-2011_11
Patent number
US08067434B2

Reaction notes

Loading…