Triphenylphosphine → 6-allyl-5-(2-(4-fluorophenyl)allyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 717795Notes

Reaction equation

Br[C:2]1[C:10]2[N:9]([CH2:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH2:13])[C:8]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:7]=3[C:6]=2[CH:5]=[C:4]([CH3:26])[CH:3]=1.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.C([Sn](CCCC)(CCCC)CCCC)C=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>[CH2:32]([C:2]1[C:10]2[N:9]([CH2:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH2:13])[C:8]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:7]=3[C:6]=2[CH:5]=[C:4]([CH3:26])[CH:3]=1)[CH:27]=[CH2:28]

Participants

Conditions

Temperature: 100 °C

Procedure

6-Bromo-5-(2-(4-fluorophenyl)allyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (185 mg, 0.23 mmol) and tetrakis(triphenylphosphine (5.3 mg, 0.046 mmol) were charged in a reaction bottle, which was evacuated and backfilled with nitrogen. Dry toluene (2 mL) was added under nitrogen and the flask purged with nitrogen for 2 min. Allyltributyltin (151 mg, 0.46 mmol) was added dropwise. The reaction mass was stirred at 100° C. overnight. The reaction mixture was concentrated under vacuum and purified on silica gel (100-200 mesh) using 0-3% MeOH:DCM as eluent. Yield: 30 mg.

Workup

customwas evacuated
additionDry toluene (2 mL) was added under nitrogen
customthe flask purged with nitrogen for 2 min
concentrationThe reaction mixture was concentrated under vacuum
custompurified on silica gel (100-200 mesh)

Sources & evidence

ORD record: ord-bd6bc47ce3094a3ea4bceb082aaf4e8c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193728B2

Reaction notes

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