Nitrogen → HCID 136195314, compound

HRID 340300Notes

Reaction equation

HRID 340300 reaction equation
C[O:2][C:3]1[CH:17]=[CH:16][C:6]2=[C:7]3[C:12](=[C:13]([NH2:15])[N:14]=[C:5]2[CH:4]=1)[N:11]=[CH:10][CH:9]=[CH:8]3.B(Br)(Br)Br.N#N>C(Cl)Cl>[NH2:15][C:13]1[C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]2[CH:16]=[CH:17][C:3]([OH:2])=[CH:4][C:5]=2[N:14]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 25134Boron tribromideHCID 44232400HCID 44232400, compound

Product 1

HCID 136195314HCID 136195314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-methoxybenzo[f][1,7]naphthyridin-5-amine (from Example 10) (1.0 eq.) in DCM (0.04 M) was added BBr3 (2.5 eq.) dropwise under N2 at −20° C. The reaction was allowed to warm to ambient temperature over 30 minutes. The reaction was then stirred overnight. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% MeOH/DCM to give 5-aminobenzo[f][1,7]naphthyridin-8-ol as a yellow solid: 1H NMR (acetone-d6): δ 8.90 (dd, 1H), 8.83 (dd, 1H), 8.32 (d, 1H), 7.83 (dd, 1H), 7.11 (br s, 2H), 7.10 (d, 1H), 6.96 (dd, 1H), 5.86 (br s, 1H). LRMS [M+H]=212.1.

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated en vacuo
  6. customto obtain a crude residue
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-1c59d6a7eabf4c0eb441224cdf0260db
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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