Tetramethyltin → HCID 68428537, compound

HRID 642274Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[C:8]2[C:14](Br)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:12]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[CH3:40][Sn](C)(C)C>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[C:8]2[C:14]([CH3:40])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:12]([CH2:23][C:24]3[CH:32]=[CH:31][C:27]4[O:28][CH2:29][O:30][C:26]=4[CH:25]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

To a mixture of 1-benzo[1,3]dioxol-5-ylmethyl-3-bromo-2-(4-chloro-phenyl)-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (from Example 38(a))(180 mg, 0.29 mmol) in DMF (2.5 mL) was added tetramethyltin (207 mg, 1.16 mmol) and Pd(PPh3)2Cl2 (30 mg, 0.044 mmol). Resulting mixture was stirred at 130° C. for 2 h. Reaction mixture was diluted with EtOAc and filtered. Filtrate was washed with water and brine, dried over MgSO4, filtered, and concentrated to give the title product 161 mg. MS-(+)-ion: M+1=549.14.

Workup

customResulting mixture
customReaction mixture
filtrationfiltered
washFiltrate was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-ab6206e5880c458f954eb0ebd51a1e1b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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