Methanol → HCID 178516887, compound

HRID 539544Notes

Reaction equation

HRID 539544 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]3[N:16]=[N:17][NH:18][CH:19]=3)=[C:9]([O:20]C)[C:8]2=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]3[N:16]=[N:17][NH:18][CH:19]=3)=[C:9]([OH:20])[C:8]2=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 178488794HCID 178488794, compound

Product 1

HCID 178516887HCID 178516887, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 158a (0.10 g, 0.338 mmol) in dry CH2Cl2 (8 mL) was slowly added 1M BBr3 (1.2 equiv) at −30° C. under argon atmosphere. The reaction mixture was stirred for 48 h at room temperature. The mixture was again cooled to −30° C. and the MeOH (5 mL) was slowly added to the mixture. After evaporation of solvent, the residue was adjusted to pH 7 with 1M NaOH and then extracted with CHCl3 (30 mL×3). The combined organic layer dried over Na2SO4 to give 79 mg (83%) of 159a as slightly brownish solid without any further purification required. 1H NMR (400 MHz, DMSO) δ 9.11 (s, 1H), 8.51 (s, 1H), 7.78 (d, J=7.3 Hz, 2H), 7.43 (t, J=7.6 Hz, 2H), 7.31 (t, J=7.3 Hz, 1H), 6.75 (d, J=5.9 Hz, 1H), 6.64 (d, J=6.0 Hz, 1H), 5.95 (t, J=7.0 Hz, 1H), 4.76 (t, J=5.5 Hz, 2H), 4.42 (t, J=5.6 Hz, 2H). 13C NMR (100 MHz, DMSO) δ 158.25, 147.17, 146.77, 131.11, 129.34, 128.41, 128.31, 125.54, 122.23, 115.38, 105.76, 49.42, 48.33. HRMS (EI) calcd for C15H14N4O2 [M]+ 282.1117. found 282.1120.

Workup

  1. customat −30° C.
  2. temperatureThe mixture was again cooled to −30° C.
  3. customAfter evaporation of solvent
  4. extractionextracted with CHCl3 (30 mL×3)
  5. dry with materialThe combined organic layer dried over Na2SO4

Sources & evidence

ORD record
ord-1d4b534d74ce49fa8df419769e30ab57
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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