5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one → HCID 68804498, compound

HRID 1878669Notes

Reaction equation

HRID 1878669 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.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[NH:32][C:31](=[O:36])[CH2:30]3)O1>>[ClH:1].[ClH:1].[N:12]12[CH2:17][CH:16]3[CH2:15][CH:14]([CH2:18][CH:10]([C@@H:9]3[O:8][C:5]3[CH:4]=[CH:3][C:2]([C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[NH:32][C:31](=[O:36])[CH2:30]5)=[N:7][CH:6]=3)[CH2:11]1)[CH2:13]2

Participants

3

Reactant 2

HCID 219314865-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-oneHCID 24986787HCID 24986787, compound

Product 1

HCID 68804498HCID 68804498, compound

Procedure

Prepared from the product of Example 15B (185 mg, 0.699 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one 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 1.93-2.00 (m, 2H), 2.23 (s, 1H), 2.39 (s, 1H), 2.43 (s, 1H), 2.56 (s, 2H), 3.58-3.78 (m, 8H), 5.09-5.16 (m, 1H), 7.10 (d, J=8.5 Hz, 1H), 7.73-7.82 (m, 2H), 8.10-8.23 (m, 2H), 8.57 (d, J=2.7 Hz, 1H). MS (DCI/NH3) m/e=362 (M+H)+. Anal. calcd. for C22H23N3O2.HCl.H2O: C, 58.64; H, 6.02; N, 9.29. Found C, 58.64; H, 5.99; N, 9.11.

Sources & evidence

ORD record
ord-79923f1982b04fe1b581718c8f0f6f70
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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