Sodium Carbonate → HCID 22048903, compound

HRID 2087239Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>O.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.COCCOC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-fluorophenylboronic acid (83.4 mg, 0.600 mmol), 7-bromo-1H-indole (98.0 mg, 0.500 mmol), LiCl (42.0 mg, 1.00 mmol), Na2CO3 (2.0 M, 0.100 mL), Pd(PPh3)4 (115 mg, 0.100 mmol) and DME (2.00 mL) was heated at 75° C. for 12 h under Argon. The resulting crude mixture was diluted with water (40 mL), the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by preparative TLC using hexane:EtOAc (8:1) to give the desired product 7-(2-fluorophenyl)-1H-indole (108 mg, 100%): 1H NMR (400 MHz, CDCl3) 8.21 (br s, 1H), 7.71 (dm, 1H, J=7.3), 7.55 (dt, 1H, J=7.3, 1.6 Hz), 7.39 (m, 1H), 7.30-7.19 (m, 5H), 6.62 (dd, 1H, J=2.1-3.3 Hz); ESMS m/e: 211.9 (M+H)+.

Workup

extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
washThe combined organic layers were washed with brine (30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by preparative TLC

Sources & evidence

ORD record: ord-596e29d1c4af4a10ac6b54710ee144bd
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727264B1

Reaction notes

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