4-methyl-1H-indol-5-amine → (4-Methyl-1H-indol-5-yl)-(2-p-tolyl-furo[3,2-b]pyridin-7-yl)-amine

HRID 1470366Notes

Reaction equation

HRID 1470366 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]([CH3:17])=[CH:13][CH:12]=3)[O:10][C:3]=12.[CH3:18][C:19]1[C:27]([NH2:28])=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2>>[CH3:18][C:19]1[C:27]([NH:28][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=4)[O:10][C:3]=23)=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2

Participants

3

Reactant 2

HCID 154344964-methyl-1H-indol-5-amineHCID 667791877-Chloro-2-(4-methylphenyl)furo[3,2-b]pyridine

Product 1

HCID 66779080(4-Methyl-1H-indol-5-yl)-(2-p-tolyl-furo[3,2-b]pyridin-7-yl)-amine

Procedure

The title compound was prepared by procedure E using 7-chloro-2-(4-methylphenyl)furo[3,2-b]pyridine (27.00 mg; 0.11 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 (17.01 mg; 0.12 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 (19 mg, 48%). (HPLC (method F): 95%, RT: 4.21 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 11.14 (s, 1H), 8.53 (s, 1H), 7.94 (d, J=5.5, 1H), 7.85 (d, J=8.1, 2H), 7.38 (t, J=2.7, 1H), 7.35 (s, 1H), 7.33-7.27 (m, 3H), 7.00 (d, J=8.4, 1H), 6.52 (s, 1H), 6.09 (d, J=5.5, 1H), 2.37 (s, 3H), 2.36 (s, 3H); MS (m/z) 354 [M+H]+, RT: 4.1 min.

Sources & evidence

ORD record
ord-cfa8613f43bc4512ae19463688b4d5cb
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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