Sodium Carbonate → HCID 178489343, compound

HRID 2196568Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][CH2:15][N:16]([CH3:24])C(=O)OC(C)(C)C)O1.Br[C:37]1[CH:53]=[C:52]([CH3:54])[C:40]2[NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[O:50][CH3:51])=[N:43][C:39]=2[CH:38]=1.[C:55](=[O:58])([O-])[O-:56].[Na+].[Na+]>COCCOC.O.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>[CH3:51][O:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[C:42]1[NH:41][C:40]2[C:52]([CH3:54])=[CH:53][C:37]([C:9]3[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=3)[CH2:12][N:13]([CH2:14][CH2:15][NH:16][CH2:24][C:55]([O:56][C:11]([CH3:32])([CH3:12])[CH3:10])=[O:58])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[CH:38][C:39]=2[N:43]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 158 (0.165 g, 0.336 mmol) in DME (1.5 mL) and water (0.5 mL) was added 159 (0.107 g, 0.336 mmol), sodium carbonate (0.107 g, 1.009 mmol) followed by Pd(Ph3P)4 (0.025 g, 0.022 mmol). The reaction mixture was degassed with nitrogen and heated to 80° C. for 16 hours. After the usual work-up the crude material was purified by silica gel chromatography (Biotage 25M, 20 to 30 to 50% ethyl acetate in hexanes) to give 160 (97.7 mg, 0.163 mmol, 48.3% yield) as yellow crusty solid. LRMS (ESI): (calc.) 600.7 (found) 601.5 (MH)+.

Workup

customThe reaction mixture was degassed with nitrogen
customAfter the usual work-up the crude material was purified by silica gel chromatography (Biotage 25M, 20 to 30 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-0cd01431ac83472a80fa748e2e439786
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338437B2

Reaction notes

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