3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carbonitrile → HCID 66760612, compound

HRID 389511Notes

Reaction equation

HRID 389511 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH:12]2[CH2:16][N:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]3)[N:14]=[CH:13]2)=[C:6]2[CH:10]=[C:9](Cl)[O:8][C:7]=12.CC1(C)C(C)(C)OB([C:34]2[C:42]3[C:37](=[CH:38][C:39]([C:43]#[N:44])=[CH:40][CH:41]=3)[NH:36][CH:35]=2)O1>>[C:23]([N:20]1[CH2:21][CH2:22][CH:17]([N:15]2[CH:16]=[C:12]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[C:7]4[O:8][C:9]([C:34]5[C:42]6[C:37](=[CH:38][C:39]([C:43]#[N:44])=[CH:40][CH:41]=6)[NH:36][CH:35]=5)=[CH:10][C:6]=34)[CH:13]=[N:14]2)[CH2:18][CH2:19]1)(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 667595393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carbonitrileHCID 66760228HCID 66760228, compound

Product 1

HCID 66760612HCID 66760612, compoundYield 60%

Procedure

The title compound was prepared in 60% yield from 1-{4-[4-(7-amino-2-chloro-furo[2,3-c]pyridin-4-yl)-4,5-dihydro-pyrazol-1-yl]-piperidin-1-yl}ethanone and 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-6-carbonitrile by a procedure analogous to Example 213. 1H NMR (600 MHz, CD3OD): δ 1.99-2.02 (m, 2H), 2.12 (s, 3H), 2.14-2.24 (m, 2H), 2.84-2.88 (m, 1H), 3.29-3.38 (m, 1H), 4.07-4.11 (m, 1H), 4.52-4.54 (m, 1H), 4.67-4.70 (m, 1H), 7.25 (s, 1H), 7.51 (d, J=7.8 Hz, 1H), 7.84 (s, 1H), 7.89 (s, 1H), 7.92 (s, 1H), 8.15 (s, 1H), 8.25 (s, 1H), 8.39 (d, J=8.0 Hz, 1H); MS (ESI): 466 [M+H]+.

Sources & evidence

ORD record
ord-b2caadb3b8cd4e96a87fdb0a6c7a96c0
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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