Carbon tetrabromide → HCID 69027125, compound

HRID 1433097Notes

Reaction equation

HRID 1433097 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15]O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:18][CH2:15][CH:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69026499HCID 69026499, compound

Product 1

HCID 69027125HCID 69027125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(6′-methoxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-yl)-methanol (300 mg, 1.35 mmol) is dissolved in methylene chloride (10 mL). carbon tetrabromide (561 mg, 1.69 mmol) is added and dissolved. The solution is cooled to 0° C. and triphenylphoshine (529 mg, 2.02 mmol) is added portionwise. The reaction is allowed to come to r.t. and is stirred for 30 min. The volume is then reduced under vacuum to ˜2 ml and purified by flash chromatography on silica gel using 2% methanol/methylene chloride as the eluent to provide 4-bromomethyl-6′-methoxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl. 1H NMR (300 MHz, CD3OD) δ 7.74 (d, 1H), 7.43 (dd, 1H), 6.72 (d, 1H), 3.83 (s, 3H), 3.54 (m, 2H), 3.38 (d, 2H), 2.65 (dt, 2H), 1.94 (m, 2H), 1.75 (m, 1H), 1.44 (m, 2H); MS (EI) 284 (M)+.

Workup

  1. dissolutiondissolved
  2. customto come to r.t.
  3. custompurified by flash chromatography on silica gel using 2% methanol/methylene chloride as the eluent

Sources & evidence

ORD record
ord-73b16ee9db064530867430a2889463bc
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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