2-(Tri-n-butylstannyl)oxazole → HCID 66919914, compound

HRID 1971707Notes

Reaction equation

HRID 1971707 reaction equation
[C:1]([N:5]1[CH2:31][CH2:30][CH2:29][C:8]2[C:9](Br)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)[C:16]([O:26][CH3:27])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:38]1[O:39][CH:40]=[CH:41][N:42]=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:1]([N:5]1[CH2:31][CH2:30][CH2:29][C:8]2[C:9]([CH:38]3[NH:42][CH2:41][CH2:40][O:39]3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)[C:16]([O:26][CH3:27])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 581248219-tert-butyl-2-pyridin-3-yl-13-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one

Product 1

HCID 66919914HCID 66919914, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 49 mg of 13d, 50 mg of 2-tributylstannyl oxazole and 10 mg of Pd(PPh3)4 in 3 ml of degassed toluene was heated under N2 at 100° C. for 48 hr. The reaction mixture was cooled and applied to a silica gel column and eluted with a gradient of toluene/ethyl acetate. The product obtained was triturated with diethyl ether to provide 15 mg of 13f as white crystalline material; Mp 218-220° C. Rf 0.20 (toluene/ethyl acetate 1/1). MS-ESI: [M+1] 482.23.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washeluted with a gradient of toluene/ethyl acetate
  3. customThe product obtained
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-ae947c1fde294d22b61417b634f63fb3
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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