Potassium Carbonate → HCID 68659477, compound

HRID 1945311Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[F:16].[Cl:17][C:18]1[C:19](B2OC(C)(C)C(C)(C)O2)=[CH:20][C:21]2[N:25]=[C:24]([O:26][C:27]3[CH:28]=[CH:29][C:30]([CH3:36])=[C:31]([CH:35]=3)[C:32]([OH:34])=[O:33])[N:23]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:22]=2[CH:45]=1>CN(C=O)C.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>[Cl:17][C:18]1[C:19]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[F:16])=[CH:20][C:21]2[N:25]=[C:24]([O:26][C:27]3[CH:28]=[CH:29][C:30]([CH3:36])=[C:31]([CH:35]=3)[C:32]([OH:34])=[O:33])[N:23]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:22]=2[CH:45]=1

Participants

Conditions

Temperature: 150 °C

Procedure

K2CO3 (0.293 mL, 0.585 mmol) followed by Pd(PPh3)4 (6.76 mg, 5.85 μmol) were added to a solution of 4-Bromo 3-fluoro anisole (0.027 mL, 0.195 mmol) and 5-[(6-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoic acid (122 mg, 0.219 mmol) in DMF (2 mL). The reaction was heated at 150° C. under microwave irradiation for 10 min. Volatiles were removed to afford the desired product, which was used in the next step without further purification.

Workup

customVolatiles were removed

Sources & evidence

ORD record: ord-2c3a4a559c0c4f38bf0c4c90dccf9ae9
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394969B2

Reaction notes

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