p-Toluenesulfonic acid → 2-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazole

HRID 2213983Notes

Reaction equation

HRID 2213983 reaction equation
B(Br)(Br)Br.[NH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13].[CH2:14]1[C:19](=[O:20])N(Br)[C:16](=[O:17])[CH2:15]1.[CH3:22][C:23](N=NC(C#N)(C)C)([C:25]#N)C.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.[C:42]([O-:45])([O-])=O.[K+].[K+].[CH3:48]C1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.CC#N.CO>[CH3:42][O:45][C:14]1[C:19]([O:20][CH3:48])=[CH:22][C:23]([C:25]2[O:12][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([CH2:13][NH:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[C:6]=3[N:5]=2)=[C:16]([OH:17])[CH:15]=1

Participants

13

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 6547AzobisisobutyronitrileHCID 11430Potassium CarbonateHCID 195092-PyridinemethanamineHCID 25134Boron tribromideHCID 67184N-bromobutanimideHCID 30141382-Amino-m-cresol

Product 1

HCID 1354286942-(4,5-Dimethoxy-2-hydroxyphenyl)-4-(2-pyridylmethyl) aminomethylbenzoxazole

Reagents, catalysts & solvents 5

HCID 241BenzeneSolvent2×HCID 887MethanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

BBr3 in CH2Cl2, rt (b) CH2OCH2Cl, TEA in CH2Cl2, rt (c) amino-m-cresol in benzene, reflux (d) BaMnO4 in benzene, reflux (e) NBS, AIBN in CCl4, reflux (f) 2-aminomethylpyridine derivative, K2CO3 in CH3CN, rt (g) TsOH in CH3OH, rt.

Sources & evidence

ORD record
ord-4c1f1f7c726e4bfb9adaa0a0ecc2be25
Source dataset
uspto-grants-2006_09
Patent number
US07105680B1

Reaction notes

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