Sodium Carbonate → HCID 24905163, compound

HRID 731820Notes

Reaction equation

[CH:1]([C:3]1[CH:20]=[CH:19][C:6]2[S:7][C:8](B3OC(C)(C)C(C)(C)O3)=[CH:9][C:5]=2[CH:4]=1)=[O:2].I[C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH2:31])[N:24]([CH:32]([CH3:34])[CH3:33])[N:23]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:31][C:29]1[N:28]=[CH:27][N:26]=[C:25]2[N:24]([CH:32]([CH3:34])[CH3:33])[N:23]=[C:22]([C:8]3[S:7][C:6]4[CH:19]=[CH:20][C:3]([CH:1]=[O:2])=[CH:4][C:5]=4[CH:9]=3)[C:30]=12

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5-Formylbenzo[b]thiophene-2-boronic acid pinacol ester (31 mg, 0.11 mmol) in EtOH (3.3 ml) was added to a solution of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.10 mmol) in DME (12 ml). Pd(PPh3)4 (30 mg, 0.03 mmol) and saturated Na2CO3 (1.9 ml) were added and the reaction was heated to 80° C. under an argon atmosphere overnight. After cooling, the reaction was extracted with saturated NaCl and CH2Cl2. Organic phases were combined, concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA42 (15.2 mg, 45% yield). ESI-MS (M+H)+ m/z calcd 338.1, found 338.0.

Workup

temperatureAfter cooling
extractionthe reaction was extracted with saturated NaCl and CH2Cl2
concentrationconcentrated in vacuo
custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)
customto yield BA42 (15.2 mg, 45% yield)

Sources & evidence

ORD record: ord-2cbba1816e6d4285952559daf4f35266
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585868B2

Reaction notes

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