Sodium Carbonate → HCID 178455331, compound

HRID 389607Notes

Reaction equation

[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[N:22][C:21]([NH2:24])=[C:20]4[O:25][C:26](Cl)=[CH:27][C:19]=34)[CH:15]=[N:14]2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:39]2[CH:47]=[C:46]3[C:42]([CH2:43][NH:44][C:45]3=[O:48])=[CH:41][CH:40]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>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>[NH2:24][C:21]1[N:22]=[CH:23][C:18]([C:16]2[CH:15]=[N:14][N:13]([C@H:10]3[CH2:11][CH2:12][C@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:30])[CH3:29])[CH2:8][CH2:9]3)[CH:17]=2)=[C:19]2[CH:27]=[C:26]([C:39]3[CH:47]=[C:46]4[C:42]([CH2:43][NH:44][C:45]4=[O:48])=[CH:41][CH:40]=3)[O:25][C:20]=12

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-{1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-1H-pyrazol-4-yl}-2-chloro-furo[2,3-c]pyridin-7-ylamine (50.0 mg, 0.112 mmol) in DME (0.894 mL) was added 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (43.5 mg, 0.168 mmol), sodium carbonate (2.0 M in water, 0.089 mL, 0.18 mmol), and Pd(PPh3)4 (20 mg, 0.02 mmol) and the reaction mixture was heated at 120° C. for 15 min in a microwave reactor. The reaction mixture was then concentrated. Purification of the residue by ISCO chromatography (0 to 5% 7 N NH3/MeOH:EtOAc) afforded 49 mg (80%) of the title compound.

Workup

concentrationThe reaction mixture was then concentrated
customPurification of the residue by ISCO chromatography (0 to 5% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record: ord-93d9932b0d744c0da03e01fdb9a5fd02
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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