4-methyl-1H-indol-5-amine → HCID 66780331, compound

HRID 1470372Notes

Reaction equation

HRID 1470372 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=3)[O:10][C:3]=12.[CH3:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2>>[CH3:20][O:19][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:31][C:30]3[C:22]([CH3:21])=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][CH:25]=[CH:24]4)[CH:8]=2)[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 66779655HCID 66779655, compound

Product 1

HCID 66780331HCID 66780331, compound

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(3,4-dimethoxyphenyl)furo[3,2-b]pyridine (29.50 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 (15.63 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 (23 mg, 57%). (HPLC (method F): 92%, RT: 3.82 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.13 (s, 1H), 8.50 (s, 1H), 7.94 (d, J=5.5, 1H), 7.52 (dd, J=8.4, 1.8, 1H), 7.38 (dd, J=10.5, 7.8, 2H), 7.31 (t, J=4.1, 2H), 7.06 (d, J=8.5, 1H), 7.01 (d, J=8.5, 1H), 6.52 (s, 1H), 6.12 (d, J=5.5, 1H), 3.82 (s, 3H), 3.76 (s, 3H), 2.37 (s, 3H); MS (m/z) 400 [M+H]+, RT: 3.6 min.

Sources & evidence

ORD record
ord-04956d024e064dfb8f5c52080d0bd4c0
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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