5-(Tributylstannyl)-1,3-thiazole → 9-tert-butyl-3-methoxy-2,14-di-1,3-thiazol-5-yl-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one

HRID 1971695Notes

Reaction equation

HRID 1971695 reaction equation
Br[C:2]1[C:3]([O:31][CH3:32])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:14]4[C:15](=[O:25])[N:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:17][CH2:18][O:19][CH2:20][C:13]=4[C:12]([C:26]4[S:30][CH:29]=[N:28][CH:27]=4)=[C:9]3[C:10]=2[CH:11]=1.C([Sn](CCCC)(CCCC)[C:38]1[S:42][CH:41]=[N:40][CH:39]=1)CCC>C1(C)C=CC=CC=1.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>[C:21]([N:16]1[C:15](=[O:25])[C:14]2[N:8]3[CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:31][CH3:32])[C:2]([C:38]5[S:42][CH:41]=[N:40][CH:39]=5)=[CH:11][C:10]=4[C:9]3=[C:12]([C:26]3[S:30][CH:29]=[N:28][CH:27]=3)[C:13]=2[CH2:20][O:19][CH2:18][CH2:17]1)([CH3:22])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 27632575-(Tributylstannyl)-1,3-thiazoleHCID 581248172-bromo-9-tert-butyl-3-methoxy-14-(1,3-thiazol-5-yl)-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-one

Product 1

HCID 581247869-tert-butyl-3-methoxy-2,14-di-1,3-thiazol-5-yl-5,6,10,11-tetrahydro-9H-[1,4]oxazocino[7',6':4,5]pyrrolo[2,1-a]isoquinolin-8(13H)-oneYield 76.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A degassed solution of 40 mg of 11i, 45 mg of 5-tributylstannyl thiazole and 15 mg of Pd(PPh3)4 in 3 ml of toluene was heated at 110° C. during 5 hr. The reaction mixture was concentrated and the residue was chromatographed over silica gel, using a gradient of toluene/acetone as eluent. The isolated product was treated with diethyl ether, to provide 31 mg of 11l as white crystalline material; Mp: 254-255° C.; Rf 0.30 (heptane/acetone 1/1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed over silica gel
  3. additionThe isolated product was treated with diethyl ether

Sources & evidence

ORD record
ord-f9e46fe6e3a34c7ebca25064663b4419
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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