Boron Trichloride → HCID 86698789, compound

HRID 338455Notes

Reaction equation

HRID 338455 reaction equation
C([O:8][CH2:9][C:10]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][C:28]=3[Cl:29])[NH:25][CH:24]=[C:23]4[C:30]([O:32][CH3:33])=[O:31])=[CH:16][CH:15]=2)[CH2:13][O:12][CH2:11]1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[Cl:29][C:28]1[CH:27]=[C:26]2[C:22]([C:23]([C:30]([O:32][CH3:33])=[O:31])=[CH:24][NH:25]2)=[CH:21][C:20]=1[C:17]1[CH:16]=[CH:15][C:14]([C:10]2([CH2:9][OH:8])[CH2:11][O:12][CH2:13]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86698788HCID 86698788, compound

Product 1

HCID 86698789HCID 86698789, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. slurry of methyl 5-[4-(3-Benzyloxymethyl-oxetan-3-yl)-phenyl]-6-chloro-1H-indole-3-carboxylate (200 mg, 0.433 mmol) in DCM (5 mL) was added boron trichloride (1.73 mL, 1.0M in DCM, 1.73 mmol) via syringe, and the mixture was allowed to warm to room temperature over five hours. The reaction mixture was concentrated to dryness, diluted with ethyl acetate (200 mL), washed with water (10 mL) and saturated brine (10 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford an orange film, which was purified by flash chromatography (12 g silica, 20-100% ethyl acetate/heptane, 38 column volumes). Product fractions were combined and concentrated in vacuo to afford the title compound as a colorless oil (40 mg, 25% yield). MS (ES+) 372 (M+H)+; 1H NMR (500 MHz, CD3OD) δ ppm 8.00-8.04 (m, 2H), 7.60 (s, 1H), 7.44-7.55 (m, 4H), 4.10 (s, 2H), 3.95-4.07 (m, 4H), 3.88 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with ethyl acetate (200 mL)
  3. washwashed with water (10 mL) and saturated brine (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford an orange film, which
  8. customwas purified by flash chromatography (12 g silica, 20-100% ethyl acetate/heptane, 38 column volumes)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a3db92264d84f48b5a1ffccdc8cbfd9
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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