2-Bromopropane → 1-Isopropyl-4-methoxy-n-(2-methyl-2-phenylpropyl)-1h-indazol-3-amine

HRID 1808310Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([NH:12][CH2:13][C:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])=[N:6][NH:7]2.C(=O)([O-])[O-].[K+].[K+].Br[CH:30]([CH3:32])[CH3:31].FC1C=CC=C(OC)C=1C=O.CO.O.C(O)(C(F)(F)F)=O>CN(C=O)C>[CH:30]([N:7]1[C:8]2[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=2)[C:5]([NH:12][CH2:13][C:14]([CH3:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])=[N:6]1)([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of Example 42 (16 mg, 0.054 mmol) in DMF (0.5 mL) was added potassium carbonate (8.3 mg, 0.06 mmol) followed by 2-bromopropane (18 uL, 0.12 mmol). Upon completion of addition, the reaction mixture was heated at 100° C. for 6 h. At the conclusion of this period, the reaction mixture was subjected to preparative HPLC (Rt=7.76 minutes using YMC ODS 5u 30×100 mm column with flow rate of 40 mL/min over 10 min period; 20 to 100% Solvent B. Solvent A=10/90/0.1% MeOH/H2O/TFA. Solvent B=90/10/0.1%) to provide Example 43 as a pink film (1.3 mg, 7%). 1H NMR (500 MHz, CDCl3) δ ppm 1.44 (s, 6H), 1.45 (s, 3H), 1.47 (s, 3H), 3.56 (s, 2H), 3.69 (s, 3H), 6.14 (d, J=7.70 Hz, 1H), 6.73 (d, J=8.80 Hz, 1H), 7.09 (t, J=7.97 Hz, 1H), 7.21-7.24 (m, 1H), 7.35 (t, J=7.70 Hz, 2H), 7.47 (d, J=8.25 Hz, 2H).

Workup

additionUpon completion of addition
customto provide Example 43 as a pink film (1.3 mg, 7%)

Sources & evidence

ORD record: ord-c4624a1a22f447ec90fed8a0c63c4555
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357809B2

Reaction notes

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