Sodium Carbonate → HCID 71208067, compound

HRID 2280248Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:18][O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]3)[N:9]=[C:10](I)[C:3]=12.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][C:37]([O:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:36][CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].B([O-])[O-]>COCCOC.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:18][O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]3)[N:9]=[C:10]([C:44]3[CH:45]=[CH:46][C:41]([O:40][C:37]4[CH:38]=[CH:39][CH:34]=[CH:35][CH:36]=4)=[CH:42][CH:43]=3)[C:3]=12

Participants

Conditions

Temperature: 75 °C

Procedure

tert-butyl 6-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1,4-oxazepane-4-carboxylate (1.18 mmol) is dissolved in ethylene glycol dimethylether (50 mL) and water (10 mL). 4,4,5,5-tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane (1.47 mmol), palladium tetrakistriphenylphosphine (0.059 mmol) and sodium carbonate (2.95 mmol) are added and the reaction is heated for 12-20 hours. Additional boronate and palladium tetrakistriphenylphosphine are added and the reaction is heated at 60-90° C. for a further 20-24 hours. The reaction is concentrated under reduced pressure. The remaining residue was partitioned between dichloromethane and water. The organic layer is dried then concentrated under reduced pressure to yield the title compound.

Workup

temperaturethe reaction is heated for 12-20 hours
concentrationThe reaction is concentrated under reduced pressure
customThe remaining residue was partitioned between dichloromethane and water
customThe organic layer is dried
concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record: ord-43cba0993caa4fc99894ff668d63a96f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09138436B2

Reaction notes

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