Diethyl Ether → N-({2-[3-(benzyloxy)prop-1-yn-1-yl]-1,3-thiazol-4-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258558

Reaction equation

HRID 1258558 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.[CH2:23]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24]#[CH:25].C(N(CC)C(C)C)(C)C.C(OCC)C>O1CCCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:27]([O:26][CH2:23][C:24]#[C:25][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N:21]([CH3:22])[N:20]=[N:19][N:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 6917484((Prop-2-yn-1-yloxy)methyl)benzeneHCID 86649974N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 86653114N-({2-[3-(benzyloxy)prop-1-yn-1-yl]-1,3-thiazol-4-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineYield 64.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenyl-methanimine (190 mg, 0.50 mmol), benzyl propargyl ether (149 mg, 1.00 mmol), copper(I) iodide (9.5 mg, 0.05 mmol), tetrakis(triphenylphosphine)palladium(0) (28.9 mg, 0.02 mmol), N,N-diisopropylethylamine (258 mg, 2.0 mmol) in degassed tetrahydrofuran (2.5 mL) was stirred under an Argon atmosphere at 50° C. for 14 h. After the addition of diethylether (2 mL) the suspension was filtered over a pad of silica gel and the filtrate was concentrated in vacuo. Purification on silica gel afforded N-({2-[3-(benzyloxy)prop-1-yn-1-yl]-1,3-thiazol-4-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine as a thick oil (144 mg, yield 62%).

Workup

  1. filtrationwas filtered over a pad of silica gel
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification on silica gel

Sources & evidence

ORD record
ord-21238b994bd64690adb48ba532ed8ee1
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Linked notes

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