Water → HCID 59425079, compound

HRID 252607Notes

Reaction equation

HRID 252607 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-d5858f75d33b4b30a8341728022ceffd
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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