2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one → HCID 178493504, compound

HRID 1778680Notes

Reaction equation

HRID 1778680 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[N:18]=[C:17]2[NH:19][N:20]=[C:21](I)[C:16]2=[CH:15][N:14]=1.[CH:23]1([N:26]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31](B4OC(C)(C)C(C)(C)O4)[CH:32]=3)[C:27]2=[O:44])[CH2:25][CH2:24]1>>[CH:23]1([N:26]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:21]4[C:16]5[C:17](=[N:18][C:13]([C:3]6[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=6[F:12])=[N:14][CH:15]=5)[NH:19][N:20]=4)[CH:32]=3)[C:27]2=[O:44])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 594023502-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 178493522HCID 178493522, compound

Product 1

HCID 178493504HCID 178493504, compound

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 4, Step 2 starting from 6-(2,6-difluoro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine and 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one. LCMS (M+H)+=464.1. 1H NMR (300 MHz, DMSO-d6) δ: 9.86 (s, 1H), 8.34 (s, 1H), 8.27 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.18 (t, J=8.3 Hz, 1H), 4.52 (s, 2H), 3.94 (s, 6H), 3.07-2.90 (m, 1H), 0.97-0.76 (m, 4H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-7688e139c5384f22ad7b10d0c40f76e8
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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