Benzyl mercaptan → HCID 86687759, compound

HRID 1473678Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([F:23])[CH2:22][O:21][CH2:20]4)=[CH:15][C:14]=3[O:24][CH3:25])=[N:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C.[CH2:77]([SH:84])[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:77]([S:84][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([F:23])[CH2:22][O:21][CH2:20]4)=[CH:15][C:14]=3[O:24][CH3:25])=[N:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1)[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The reaction mixture from step 4 was treated with Pd2(dba)3 (0.023 g, 0.025 mmol), Xantphos (0.029 g, 0.051 mmol), and n,n-diisopropylethylamine (0.530 ml, 3.04 mmol), and was heated to 60° C. Benzyl mercaptan (0.120 ml, 1.012 mmol) was added, and the reaction mixture was allowed to stir for one hour at 60° C. LC/MS showed mostly product, so the reaction mixture was concentrated. Purification of the crude residue by silica gel column chromatography (0-75% EtOAc/heptane) gave 7-(benzylthio)-4-(4-(3-fluorooxetan-3-yl)-2-methoxyphenyl)-2-methylquinazoline (0.189 g, 0.423 mmol, 41.8% yield) with minor impurities. (M+H)+=447.0.

Workup

concentrationso the reaction mixture was concentrated
customPurification of the crude residue by silica gel column chromatography (0-75% EtOAc/heptane)

Sources & evidence

ORD record: ord-2157565336c745e18473f4db2dcefcf8
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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