Carbon tetrabromide → HCID 59504622, compound

HRID 2400566Notes

Reaction equation

HRID 2400566 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26]O)=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1.[Br:28]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:28][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[N:16]=[C:15]([C:4]3[CH:3]=[C:2]([CH3:1])[N:6]([CH2:7][C:8]4[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=4)[N:5]=3)[O:19][N:18]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59504738HCID 59504738, compound

Product 1

HCID 59504622HCID 59504622, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of (4-{5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol (Example 110, 1.50 g, 4.16 mmol) in dichloromethane (60 mL) was added tetrabromomethane (1.66 g, 5.00 mmol) and triphenyl-phosphane (1.64 g, 6.24 mmol). The mixture was stirred at rt for 5 h and then partly concentrated under reduced pressure. The solid formed was filtered off and dried under reduced pressure to yield the title compound. The filtrate was concentrated and purified by MPLC (silica, cyclohexane/ethyl acetate 9:1) to afford another batch of the title compound (combined 1.55 g, 88%): 1H-NMR (400 MHz, DMSO-d6) δ 8.07 (d, 2H), 7.66 (d, 2H), 7.17 (d, 2H), 7.12 (d, 2H), 6.90 (s, 1H), 5.42 (s, 2H), 4.70 (s, 2H), 2.32 (s, 3H). 2.28 (s, 3H); ES-MS m/z 423 (MH)+; HPLC RT (Method D) 3.05 min.

Workup

  1. concentrationpartly concentrated under reduced pressure
  2. customThe solid formed
  3. filtrationwas filtered off
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d01bf40145eb438aa980d9864fca8a8b
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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