4-Butylphenylboronic acid → HCID 16047072, compound

HRID 1690704Notes

Reaction equation

HRID 1690704 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([OH:15])=[O:14])=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([NH:33]N)[C:28]=2[F:35])=[CH:23][CH:22]=1)[CH2:18][CH2:19][CH3:20].C(C1C=CC(B(O)O)=CC=1)CCC>>[CH2:17]([C:21]1[CH:22]=[CH:23][C:24]([C:27]2[C:28]([F:35])=[C:29]3[C:30]([C:3]4[CH2:4][CH2:5][CH2:6][C:7]5[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][C:8]=5[C:2]=4[NH:33]3)=[CH:31][CH:32]=2)=[CH:25][CH:26]=1)[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 3

HCID 41008604-Butylphenylboronic acidHCID 669048333470-47-1HCID 66904900HCID 66904900, compound

Product 1

HCID 16047072HCID 16047072, compoundYield 34%

Procedure

The title material is prepared in 34% yield by reacting 5-Oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxylic acid (J. Org. Chem. 1962, 27(1), p 70-76) and (4′-Butyl-2-fluoro-biphenyl-3-yl)-hydrazine hydrochloride (prepared as in example 69, steps 1 and 2 except using 4-n-butylphenylboronic acid as the coupling partner) in an analogous manner to example 1, step 3 except that purification is accomplished by reverse phase mass triggered HPLC: 1H NMR (Acetone-d6) δ 10.72 (bs, 1H), 8.09 (d, 1H), 7.99 (d, 1H), 7.92 (s, 1H), 7.58 (d, 2H), 7.45 (d, 1H), 7.31 (d, 2H), 7.17 (dd, 1H), 3.18 (t, 2H), 3.10-3.04 (m, 2H), 2.72 (t, 2H), 2.22-2.14 (m, 2H), 1.73-1.64 (m, 2H), 1.45-1.38 (m, 2H), 0.96 (t, 3H); LC/MS calculated for [M+H]+ C28H26FNO2: 428.2, found: 428.2.

Workup

  1. customprepared as in example 69, steps 1 and 2
  2. customexcept that purification

Sources & evidence

ORD record
ord-649b0ee705cd4e7eae280dfb3a63947f
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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