Sodium Carbonate → HCID 131734996, compound

HRID 923662Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[N:7]([CH:9]([C:11](=[O:33])[NH:12][C:13]1[CH:18]=[C:17](Br)[C:16]([Cl:20])=[C:15]([C:21]#[C:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:35][N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][C:43]=2B(O)O)[CH:38]=[N:37]1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:9]([C:11](=[O:33])[NH:12][C:13]1[CH:18]=[C:17]([C:43]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:44]=2[N:36]([CH3:35])[N:37]=[CH:38]3)[C:16]([Cl:20])=[C:15]([C:21]#[C:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (20 mg, 0.03 mmol) is added to a mixture of tert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate C2 (82 mg, 0.14 mmol), (1-methyl-1H-indazol-7-yl)boronic acid (24 mg, 0.14 mmol), Na2CO3 (44 mg, 0.42 mmol), dioxane (0.8 ml) and water (0.2 ml) under argon atmosphere and stirred at 100° C. for 4 h. The mixture is diluted with water (10 ml) and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 25 mg (28%). HPLC-MS: M+H=624; tR=1.94 min (METHOD—1).

Workup

extractionextracted with EtOAc
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated in vacuo
customThe product is purified by RP HPLC

Sources & evidence

ORD record: ord-1c681887f67341188b475b9338c8185f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278978B2

Reaction notes

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