Allyltributylstannane → HCID 67540187, compound

HRID 579678Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:20]4[C:25]([C:26]=2[CH:27]=1)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:9][CH:8]=3.[CH2:36]([Sn](CCCC)(CCCC)CCCC)[CH:37]=[CH2:38].[Li+].[Cl-]>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.C1COCC1>[CH2:38]([C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:20]4[C:25]([C:26]=2[CH:27]=1)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:9][CH:8]=3)[CH:37]=[CH2:36]

Participants

Conditions

Temperature: 90 °C

Procedure

THF (20 ml) was added into a mixture of 5 (0.62 g, 1.18 mmol), allyltributyltin (0.78 g, 2.36 mmol), Pd(PPh3)4 (0.068 g, 0.06 mmol) and LiCl (0.092 g, 3.54 mmol). The reaction mixture was stirred at 90° C. for 24 hours. After evaporating off the solvent, the crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 4:1 (v/v) as the eluent to yield 6 (0.35 g, 61%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 8.40-8.38 (dd, 2H), 8.19-8.17 (d, 1H), 8.00 (s, 1H), 7.93-7.79 (m, 2H), 7.50-7.41 (m, 4H), 7.34-7.22 (m, 3H), 6.18-6.08 (m, 1H), 5.20-5.10 (m, 2H), 4.15-4.11 (m, 4H), 3.61-3.59 (d, 2H), 2.50-2.39 (m, 2H), 1.03-1.01 (m, 12H).

Workup

customAfter evaporating off the solvent
customthe crude product was purified by gradient column chromatography on silica gel with hexane/methylene chloride 9:1 to 4:1 (v/v) as the eluent

Sources & evidence

ORD record: ord-cd7c87ed7e7e4f22a727e7b213fc1129
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040718B2

Reaction notes

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