Water → HCID 19780354, compound

HRID 2081684Notes

Reaction equation

C[O:2][C:3]1[C:4]([CH3:23])=[C:5]2[C:19](=[CH:20][C:21]=1[CH3:22])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:15]=3[C:7]=1[CH2:6]2.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[C:4]([CH3:23])=[C:5]2[C:19](=[CH:20][C:21]=1[CH3:22])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:15]=3[C:7]=1[CH2:6]2

Participants

Conditions

Temperature: -78 °C

Procedure

5,10-Dihydro-2-methoxy-1,3-dimethyl-8-isopropylindeno[1,2-b]indole (0.50 g, 1.64 mmol) was dissolved in dry dichloromethane (DCM, 2 cm3) under anhydrous conditions and cooled to -78° C. Boron tribromide (2 cm3 1.2 eq of 1 M solution in DCM) was added, and warmed to room temperature, whereupon a suspension formed. After 20 minutes, this had re-dissolved. Water (2 cm3) was cautiously added, and the mixture extracted between more DCM, and saturated sodium bicarbonate solution (some solid around during extraction finally dissolved). The DCM layer was dried (Na2SO4) and filtered through a pad of "flash" silica, eluting with DCM to yield a white solid (0.43 g, 90%) M.p. 173° C.(dec.). 1H NMR (CDCl3)δ: 8.04 (1H, br), 7.43 (1H, br), 7.29 (1H, d, J=8.2), 7.04 (1H, br), 4.58 (1H, br), 3.55 (2H, br), 30.2 (1H, septet, J=7.0Hz, 2.30 (3H, s), 2.29 (3H,s), 1.33 (6H, d, J=7.0Hz).

Workup

temperaturewarmed to room temperature, whereupon a suspension
customformed
dissolutionthis had re-dissolved
extractionthe mixture extracted between more DCM, and saturated sodium bicarbonate solution (some solid
extractionaround during extraction
dissolutionfinally dissolved)
dry with materialThe DCM layer was dried (Na2SO4)
filtrationfiltered through a pad of "flash" silica
washeluting with DCM

Sources & evidence

ORD record: ord-7b71edbc222e4edd8f4778d263865981
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05185360

Reaction notes

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