9-Iodo-9-borabicyclo(3.3.1)nonane → 7-Isopropyl-5-[isopropyl-(4-hydroxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

HRID 2290156Notes

Reaction equation

HRID 2290156 reaction equation
[CH:1]([C:4]1[C:12]2[O:11][CH2:10][C:9]([CH3:14])([CH3:13])[C:8]=2[CH:7]=[C:6]([N:15]([CH:24]([CH3:26])[CH3:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[C:5]=1[CH3:27])([CH3:3])[CH3:2].IB1C2CCCC1CCC2>ClCCl>[CH:1]([C:4]1[C:12]2[O:11][CH2:10][C:9]([CH3:13])([CH3:14])[C:8]=2[CH:7]=[C:6]([N:15]([CH:24]([CH3:26])[CH3:25])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[C:5]=1[CH3:27])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5782319-Iodo-9-borabicyclo(3.3.1)nonaneHCID 186991727-Isopropyl-5-[isopropyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran2×

Product 1

HCID 186991777-Isopropyl-5-[isopropyl-(4-hydroxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuranYield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following general procedure M and using 7-isopropyl-5-[isopropyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 55, 0.077 g, 0.21 mmol) and 1M solution of 9-iodo-9-borabicyclo[3.3.1]nonane (B-iodo-9-BBN) in hexanes (0.25 mL, 0.25 mmol) in 2 mL of anhydrous dichloromethane, the title compound (0.06 g, 77%) was obtained as a brown oil that was used in the next step without further purification.

Sources & evidence

ORD record
ord-a4642bb13d524202b741abf56fa769ce
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

Loading…