4-methyl-1H-indol-5-amine → HCID 66779741, compound

HRID 1470371Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=3)[O:10][C:3]=12.[CH3:19][C:20]1[C:28]([NH2:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2>>[CH3:18][C:13]1[CH:12]=[C:11]([C:9]2[O:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[NH:29][C:28]3[C:20]([CH3:19])=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][CH:23]=[CH:22]4)[CH:8]=2)[CH:16]=[C:15]([CH3:17])[CH:14]=1

Participants

Reactant 2

HCID 154344964-methyl-1H-indol-5-amine

HCID 66779579HCID 66779579, compound

Product 1

HCID 66779741HCID 66779741, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(3,5-dimethylphenyl)furo[3,2-b]pyridine (26.00 mg; 0.10 mmol; 1.00 eq.) instead of 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine, and 4-methyl-1H-indol-5-ylamine (15.49 mg; 0.11 mmol; 1.05 eq.) instead of 6-amino-2,2-difluoro-4H-benzo[1,4]oxazin-3-one, and was obtained as a beige solid (25 mg, 67%). (HPLC (method F): 96%, RT: 4.45 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.15 (s, 1H), 8.54 (s, 1H), 7.95 (d, J=5.5, 1H), 7.50 (s, 2H), 7.38 (t, J=2.7, 1H), 7.33 (s, 1H), 7.31 (d, J=8.4, 1H), 7.08-6.95 (m, 2H), 6.52 (s, 1H), 6.14 (d, J=5.5, 1H), 2.36 (s, 3H), 2.30 (s, 6H); MS (m/z) 368 [M+H]+, RT: 4.3 min.

Sources & evidence

ORD record: ord-5c1d412ecaa84ec6b40af5a44b56c8bb
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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