Hydrochloric Acid → 4-(2-Methylbenzo[b]thiophen-5-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 402097

反応式

HRID 402097 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH3:10])=[CH:7][C:6]=2[CH:11]=1.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](B(O)O)=[CH:14][N:13]=1.Cl.[CH2:26](OCC)C>C(OCC)(=O)C>[CH3:10][C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([CH:15]3[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:12][N:13]([CH3:26])[CH2:14]3)=[CH:11][C:6]=2[CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3761204Isoquinoline-4-boronic acidHCID 136630355-Bromo-2-methyl-1-benzothiophene

生成物 1

HCID 689949174-(2-Methylbenzo[b]thiophen-5-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

4-(2-methylbenzo[b]thiophen-5-yl)-2-methyl-1,2,3,4-tetrahydroisoquinoline was prepared from 5-bromo-2-methylbenzothiophene and isoquinolin-4-ylboronic acid as described in Example 40 (Steps C to E). The free base was dissolved in ethyl acetate and treated with 2 M hydrogen chloride in diethyl ether (2 equiv) to give the corresponding hydrochloride salt (0.41 g, 98.8% AUC HPLC): 1H NMR (300 MHz, DMSO-d6) δ 11.09 (br s, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.63 (s, 1H), 7.09-7.27 (m, 5H), 6.76 (d, J=7.5 Hz, 1H), 4.69 (dd, J=10.8, 6.3 Hz, 1H), 4.55 (br s, 2H), 3.54-3.83 (m, 2H), 2.94 (s, 1H), 2.57 (s, 3H); EI MS m/z=293 [C19H19NS]+. Anal. Calcd. for C19H20ClNS: C, 68.61; H, 6.10; N, 4.21 with 0.73% H2O. Found: C, 68.35; H, 6.55; N, 4.00.

出典と根拠

ORDレコード
ord-56fa937dfc4b46dab612f5241f157f29
出典データセット
uspto-grants-2014_06
特許番号
US08741901B2

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