Boron tribromide → 4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol

HRID 1259129Notes

Reaction equation

HRID 1259129 reaction equation
C[O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][CH2:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[C:16]2[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:15]2=[N:14][C:13]=3[NH2:24])=[C:5]([CH3:27])[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:24][C:13]1[C:12]2[N:11]=[CH:10][C:9]([CH2:8][CH2:7][C:6]3[CH:25]=[CH:26][C:3]([OH:2])=[CH:4][C:5]=3[CH3:27])=[CH:18][C:17]=2[C:16]2[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 498381322-(4-Methoxy-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 581665094-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-(4-methoxy-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (Example 49) in methylene chloride (0.2 M) in an ice-water bath was added 1 N solution of BBr3 (2 eq) in CH2Cl2 in a drop-wise fashion. In 30 minutes the reaction was quenched with methanol and was concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% methanol in dichloromethane to give 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenol as a white solid. 1H NMR (DMSO-d6): δ 8.99 (s, 1H), 8.75 (d, 1H), 8.60 (d, 1H), 8.27 (d, 1H), 7.28 (s, 1H), 7.09 (dd, 1H), 6.99 (bs, 2H), 6.88 (d, 1H), 6.49 (d, 1H), 6.42 (dd, 1H), 3.02-2.96 (dd, 2H), 2.86-2.81 (dd, 2H), 2.38 (s, 3H), 2.13 (s, 3H). LRMS [M+H]=344.2

Workup

  1. customIn 30 minutes the reaction was quenched with methanol
  2. concentrationwas concentrated en vaccuo
  3. customto obtain a crude residue
  4. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-f4283faf1ec14c659f70db662f339405
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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