Diethyl Ether → 9-tert-butyl-3-methoxy-2-pyrazin-2-yl-15-(1,3-thiazol-5-yl)-5,6,9,10,11,12-hexahydro[1,5]oxazonino[8',7':4,5]pyrrolo[2,1-a]isoquinolin-8(14H)-one

HRID 1971665Notes

Reaction equation

HRID 1971665 reaction equation
Br[C:2]1[C:3]([O:32][CH3:33])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:14]4[C:15](=[O:26])[N:16]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][CH2:18][CH2:19][O:20][CH2:21][C:13]=4[C:12]([C:27]4[S:31][CH:30]=[N:29][CH:28]=4)=[C:9]3[C:10]=2[CH:11]=1.C([Sn](CCCC)(CCCC)[C:39]1[CH:44]=[N:43][CH:42]=[CH:41][N:40]=1)CCC.C(OCC)C>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:22]([N:16]1[C:15](=[O:26])[C:14]2[N:8]3[CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:32][CH3:33])[C:2]([C:39]5[CH:44]=[N:43][CH:42]=[CH:41][N:40]=5)=[CH:11][C:10]=4[C:9]3=[C:12]([C:27]3[S:31][CH:30]=[N:29][CH:28]=3)[C:13]=2[CH2:21][O:20][CH2:19][CH2:18][CH2:17]1)([CH3:23])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 27373162-(Tributylstannyl)pyrazineHCID 58124867HCID 58124867, compound

Product 1

HCID 509389769-tert-butyl-3-methoxy-2-pyrazin-2-yl-15-(1,3-thiazol-5-yl)-5,6,9,10,11,12-hexahydro[1,5]oxazonino[8',7':4,5]pyrrolo[2,1-a]isoquinolin-8(14H)-oneYield 88.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 75 mg of 8e, 150 mg of 2-tributylstannylpyrazine and 16 mg of Pd(PPh3)4 in 2 ml of degassed toluene was heated under N2 atmosphere for 24 hr. The reaction mixture was concentrated and the crude material was chromatographed over silica gel, using a gradient of toluene/acetone. The material isolated was treated with diethyl ether and provided 66 mg of 8g; Mp 235-236° C.; MS-ESI: [M+1] 530.3;

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude material was chromatographed over silica gel
  3. customThe material isolated

Sources & evidence

ORD record
ord-90139107563843cc8ded9f0f0d720cc5
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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