5-Indolylboronic acid → HCID 86621402, compound

HRID 1878667Notes

Reaction equation

HRID 1878667 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][C:24](B(O)O)=[CH:25][CH:26]=2)[CH:21]=[CH:20]1>>[ClH:1].[ClH:1].[NH:19]1[C:27]2[C:22](=[CH:23][C:24]([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:25][CH:26]=2)[CH:21]=[CH:20]1

Participants

3

Reactant 2

HCID 27343615-Indolylboronic acidHCID 24986787HCID 24986787, compound

Product 1

HCID 86621402HCID 86621402, compound

Procedure

Prepared from the product of Example 15B (165 mg, 0.623 mmol) and IT-indol-5-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 1.96 (s, 1H), 2.00 (s, 1H), 2.24 (s, 1H), 2.40 (s, 1H), 2.44 (s, 1H), 2.59 (s, 2H), 3.61 (s, 2H), 3.74 (s, 4H), 5.19 (t, J=3.2 Hz, 1H), 6.66 (dd, J=3.2, 0.8 Hz, 1H), 7.43 (d, J=3.4 Hz, 1H), 7.59-7.64 (m, 1H), 7.64-7.68 (m, 1H), 8.16 (dd, J=1.9, 0.8 Hz, 1H), 8.31-8.35 (m, 1H), 8.36-8.41 (m, 1H), 8.61 (d, J=2.0 Hz, 1H). MS (DCI/NH3) m/e=346 (M+H)+. Anal. calcd. for C22H23N3O.2HCl.H2O: C, 60.55; H, 6.24; N, 9.63. Found C, 60.71; H, 6.38; N, 9.39.

Sources & evidence

ORD record
ord-84894b6b89354f04bfbe18e1b82bc979
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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