1H-Indol-6-ylboronic acid → HCID 86621403, compound

HRID 1878668Notes

Reaction equation

HRID 1878668 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C@@H:9]2[CH:16]3[CH2:17][N:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)=[CH:4][CH:3]=1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25](B(O)O)[CH:26]=2)[CH:21]=[CH:20]1>>[ClH:1].[ClH:1].[ClH:1].[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:2]3[N:7]=[CH:6][C:5]([O:8][C@@H:9]4[CH:16]5[CH2:17][N:12]6[CH2:13][CH:14]([CH2:18][CH:10]4[CH2:11]6)[CH2:15]5)=[CH:4][CH:3]=3)[CH:26]=2)[CH:21]=[CH:20]1

Participants

3

Reactant 2

HCID 27632051H-Indol-6-ylboronic acidHCID 24986787HCID 24986787, compound

Product 1

HCID 86621403HCID 86621403, compound

Procedure

Prepared from the product of Example 15B (115 mg, 0.434 mmol) and 1H-indol-6-ylboronic acid using the microwave Suzuki coupling Method G and the salt formation Method H to provide the titled compound: 1H NMR (300 MHz, methanol-D4) δ ppm 1.93-2.05 (m, 2H), 2.24 (s, 1H), 2.40 (s, 1H), 2.44 (s, 1H), 2.59 (s, 2H), 3.61 (s, 2H), 3.67-3.81 (m, 4H), 5.19 (t, J=3.2 Hz, 1H), 6.61 (d, J=3.1 Hz, 1H), 7.48-7.55 (m, 2H), 7.82 (d, J=8.5 Hz, 1H), 7.97 (s, 1H), 8.31-8.36 (m, 1H), 8.36-8.42 (m, 1H), 8.62 (d, J=2.4 Hz, 1H). MS (DCI/NH3) m/e=346 (M+H)+. Anal. calcd. for C22H23N3O.3 HCl.0.3H2O: C, 57.42; H, 5.83; N, 9.13. Found C, 57.46; H, 5.98; N, 9.01.

Sources & evidence

ORD record
ord-adcbe936a194486399a8c9b3b17e88e3
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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