Water → HCID 22859568, compound

HRID 1441080Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:11]=[C:10]2[CH2:26][C@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH3:32].[CH2:33]([Sn:37](Cl)([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH3:36].O>O1CCCC1>[CH3:32][N:28]1[CH2:29][CH2:30][CH2:31][C@@H:27]1[CH2:26][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([Sn:37]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:33][CH2:34][CH2:35][CH3:36])[CH:8]=2)[N:12]([Si:16]([CH:17]([CH3:19])[CH3:18])([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:25])[CH3:24])[CH:11]=1

Participants

Conditions

Temperature: -70 °C

Procedure

n-ButylLithium (7.80 ml of a 2.5M solution in hexanes, 19.49 ml) was added dropwise to a solution of 5-bromo-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1-triisopropylsilylindole (6.28 g, 13.97 mmol) (Preparation 58) in tetrahydrofuran (430 ml) at -78° C. The reaction was then stirred at -70° C. for 1/2 hour whereupon tri-n-butylstannylchloride (3.97 ml, 4.64 mmol) was added and the reaction stirred at -70° C. for 20 minutes. The reaction was then warmed to room temperature and 14.4 ml of water was added and the resulting solution partitioned (971/2:21/2) to afford, after combination and evaporation of the appropriate fractions, the title compound as an oil. Found: C,70.29; H,8.72; N,8.17. C30H43N3O2Si.1/8CH2Cl2 requires: C,70.07; H,8.44; N,8.14%.

Workup

additionwas added
temperatureThe reaction was then warmed to room temperature
customthe resulting solution partitioned (971/2:21/2)
customto afford
customafter combination and evaporation of the appropriate fractions

Sources & evidence

ORD record: ord-8ec29ebb24c6495392fa521f5d160243
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05502065

Reaction notes

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