4-Iodophenol → tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-(4-iodophenoxy)propyl)thiazole-4-carboxylate

HRID 1518308ノート

反応式

HRID 1518308 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:35][CH2:36][CH2:37][OH:38])=[C:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:66][C:67]1[CH:72]=[CH:71][C:70](O)=[CH:69][CH:68]=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:44])([CH3:45])[CH3:46])[C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:35][CH2:36][CH2:37][O:38][C:70]3[CH:71]=[CH:72][C:67]([I:66])=[CH:68][CH:69]=3)=[C:26]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

参加物

6

反応物 4

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 59447663tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate

生成物 1

HCID 59447531tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-(4-iodophenoxy)propyl)thiazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-carboxylate (92 mg, 0.135 mmol), triphenylphosphine (35.4 mg, 0.135 mmol) and 4-iodophenol (29.7 mg, 0.135 mmol) in THF (2 mL) was added DBAD (32 mg, 0.135 mmol). The mixture was stirred at rt for 4 hours. LC/MS showed the expected product as a single peak. The mixture was diluted with EtOAc and washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 3% EtOAc in hexanes to provide 110 mg (92%) of the desired product: 1H NMR (300 MHz, CDCl3) δ ppm 8.30 (1H, m), 7.72 (1H, d), 7.54 (4H, m), 7.34 (3H, m), 6.67 (2H, d), 6.00 (2H, s), 5.14 (2H, s), 3.96 (4H, m), 3.75 (2H, t), 3.22 (2H, t), 3.06 (2H, t), 2.13 (2H, m), 1.59 (9H, s), 0.97 (2H, t), 0.01 (9H, m). MS (ESI(+)): m/z 833 (M+H).

出典と根拠

ORDレコード
ord-8df876d16c4c4f4b8e36125f7deeb455
出典データセット
uspto-grants-2012_07
特許番号
US08232273B2

反応ノート

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