Water → HCID 59425079, compound

HRID 506120Notes

Reaction equation

HRID 506120 reaction equation
[CH:1]([O:4][C:5](=[O:30])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24]C)[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].B(Br)(Br)Br.O>C(Cl)Cl>[CH:1]([O:4][C:5](=[O:30])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH:26]3[CH2:29][CH2:28][CH2:27]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([OH:24])[CH:16]=3)=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 49772094HCID 49772094, compound

Product 1

HCID 59425079HCID 59425079, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution [4-(3-cyano-1-cyclobutyl-6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (950 mg, 2.35 mmol) in DCM (10 mL) is added BBr3 (556 uL, 5.9 mmol) over a period of 20 min. The reaction mixture is stirred further for 1 h at room temperature and then water (1 mL) is added. The solvents are removed under reduced pressure. The residue is dissolved in MeOH and then poured into cold water. The precipitate is collected by filtration and washed with hexane and dried in vacuo to afford [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (650 mg, 71%).

Workup

  1. customThe solvents are removed under reduced pressure
  2. dissolutionThe residue is dissolved in MeOH
  3. additionpoured into cold water
  4. filtrationThe precipitate is collected by filtration
  5. washwashed with hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-097cd01f4057427f8b7184608f305c5f
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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