Boron tribromide → 4-[3-(4-Chloro-phenyl)-5,6,7,8-tetrahydro-4H-1,2,6-triaza-azulen-1-ylmethyl]-benzene-1,2-diol

HRID 599971Notes

Reaction equation

HRID 599971 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][C:32]=1[O:33]CC1C=CC=CC=1)[CH2:12][N:13]1[C:22]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][C:16]=2[C:15]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[N:14]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:15]2[C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:22]=3[N:13]([CH2:12][C:11]3[CH:10]=[C:9]([OH:8])[C:32]([OH:33])=[CH:31][CH:30]=3)[N:14]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59752681HCID 59752681, compound

Product 1

HCID 597525614-[3-(4-Chloro-phenyl)-5,6,7,8-tetrahydro-4H-1,2,6-triaza-azulen-1-ylmethyl]-benzene-1,2-diolYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(3,4-bis-benzyloxy-benzyl)-3-(4-chloro-phenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene-carboxylic acid tert-butyl ester (Example 154, 0.1 mmol) in CH2Cl2 (5 mL) was cooled to 0° C., and 1 M BBr3 in CH2Cl2 (0.5 mL) was added. The mixture was allowed to warm to RT and was stirred at RT for 1 h. The precipitate that had formed was collected by filtration, washed with water, and dried under vacuum to provide the title compound (25 mg). MS (ESI): exact mass calculated for C20H20ClN3O2, 369.12. found, m/z 370.0 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.44-7.42 (m, 4H), 7.39-7.37 (m, 2H), 6.63 (d, J=8.1 Hz, 1H), 6.50 (d, J=2.1 Hz, 1H), 6.45 (dd, J=8.1, 2.1 Hz, 1H), 5.18 (s, 2H), 3.29-3.25 (m, 4H), 3.06-3.04 (m, 2H), 2.97-2.95 (m, 2H).

Workup

  1. customThe precipitate that had formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8df02d2173134f4f9b893465e3c02717
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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