Ethyl Acetate → N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-N'-(4'-methylbiphenyl-3-yl)urea

HRID 1922537Notes

Reaction equation

[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=3)=[O:14])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[C:23]1([CH3:32])[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+].C(OC(=O)C)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13]([NH:15][C:16]3[CH:17]=[C:18]([C:26]4[CH:27]=[CH:28][C:23]([CH3:32])=[CH:24][CH:25]=4)[CH:19]=[CH:20][CH:21]=3)=[O:14])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

Next, to a solution of N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-N′-(3-iodophenyl)urea (9.0 mg, 0.02 mmol) and 4-tolylboronic acid (3.60 mg, 0.03 mmol) in THF was added tetrakis(triphenylphosphine)palladium(0) (2.55 mg) followed by 0.1 mL of saturated sodium bicarbonate solution. The mixture was stirred for 3 hours at 90° C., then ethylacetate was added. The mixture was passed through a short pad of silica gel and was concentrated under reduced pressure to afford N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)-N′-(4′-methylbiphenyl-3-yl)urea (2.80 mg, 34% yield).

Workup

concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-5c0e7d0e75494a2a9df7820a9d464419
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173841B2

Reaction notes

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