Diisopropylethylamine → 3-{1-[(3-fluoro-5-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-amine

HRID 1909989Notes

Reaction equation

HRID 1909989 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:14]4[C:15]([NH2:19])=[N:16][CH:17]=[CH:18][C:13]=4[O:12][CH:11]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29](O)=[O:30])[CH:24]=[C:25]([CH3:27])[CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C)C=O.O>[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C:29]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]4[C:14]5[C:15]([NH2:19])=[N:16][CH:17]=[CH:18][C:13]=5[O:12][CH:11]=4)=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:30])[CH:24]=[C:25]([CH3:27])[CH:26]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27784543-Fluoro-5-methylphenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668234823-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine

Product 1

HCID 668235823-{1-[(3-fluoro-5-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-amineYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (150 mg, 0.440 mmol), 3-fluoro-5-methylphenylacetic acid (78 mg, 0.464 mmol), HATU (184 mg, 0.484 mmol), and Hunig's base (0.31 mL, 1.775 mmol) in N,N-Dimethylformamide (DMF) (3 mL) was stirred at room temperature for 4 days. Water (10 mL) was added, the mixture was stirred for about 4 hours, and the precipitate was collected by vacuum filtration. The solid was dried in the vacuum oven overnight to give 3-{1-[(3-fluoro-5-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-amine (164 mg, 0.388 mmol, 88% yield) as a tan solid. LC/MS (ES) m/z=402 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H), 3.24 (t, J=8.46 Hz, 2H), 3.87 (s, 2H), 4.24 (t, J=8.59 Hz, 2H), 5.53 (s, 2H), 6.90-7.00 (m, 4H), 7.30 (d, J=8.34 Hz, 1H), 7.39 (s, 1H), 7.86 (d, J=5.81 Hz, 1H), 7.92 (s, 1H), 8.17 (d, J=8.34 Hz, 1H).

Workup

  1. stirringthe mixture was stirred for about 4 hours
  2. filtrationthe precipitate was collected by vacuum filtration
  3. customThe solid was dried in the vacuum oven overnight

Sources & evidence

ORD record
ord-92ffaaaeb8e849678531e650779627fe
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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