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 1518308Notes

Reaction equation

HRID 1518308 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Sources & evidence

ORD record
ord-8df876d16c4c4f4b8e36125f7deeb455
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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