Toluene → HCID 86601243, compound

HRID 2251965Notes

Reaction equation

HRID 2251965 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=1)=[N+:2]=[N-:3].[CH2:19]([Sn:23]([C:32]#[C:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].C1(C)C=CC=CC=1>>[F:18][C:15]([F:16])([F:17])[C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([C:11]([F:13])([F:14])[F:12])[CH:8]=1)[CH2:4][N:1]1[C:33]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[C:32]([Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])[N:3]=[N:2]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 135811644-Tributylstannanylethynyl-morpholineHCID 441857431-(Azidomethyl)-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 86601243HCID 86601243, compoundYield 66%

Conditions

Temperature
100 °C

Procedure

Add 1-azidomethyl-3,5-bis-trifluoromethyl-benzene (1.21 g, 4.5 mmol) to a solution of 4-tributylstannanylethynyl-morpholine in toluene (5 mL) (1.20 g, 3.0 mmol). See Berger, D., et al., Helv. Chim. Acta (1996) 79(I): 179-91. Flush with N2, seal in reaction vessel, and heat at 100° C. overnight. Concentrate, dissolve residue in CHCl3, dry over MgSO4, concentrate. Purify by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford the title compound (710 mg, 66%); MS(IS) 669 (M+1); TLC: Rf=0.53 (25% EtOAc/hexanes).

Workup

  1. customFlush with N2
  2. customseal in reaction vessel
  3. concentrationConcentrate
  4. dissolutiondissolve residue in CHCl3
  5. dry with materialdry over MgSO4
  6. concentrationconcentrate
  7. customPurify by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-37269fba170d4de699b26db9ac681871
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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