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Toluene → 5,6-Disubstituted anthranilic acid sulfonamide, 9e

HRID 1725928
ノート
印刷プレビュー

反応式

HRID 1725928 の反応式
Br[C:2]1[C:3]([CH3:29])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:38](B(O)O)[CH2:39][CH2:40][CH3:41].C1(C)C=CC=CC=1>C(OCC)(=O)C.C1(P([Pd](Cl)(Cl)P(C2CCCCC2)(C2CCCCC2)C2CCCCC2)(C2CCCCC2)C2CCCCC2)CCCCC1.O>[CH2:38]([C:2]1[C:3]([CH3:29])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:20])=[O:21])=[CH:16][CH:17]=1)[C:5]([OH:7])=[O:6])[CH2:39][CH2:40][CH3:41]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1140TolueneHCID 20479Butylboronic AcidHCID 62657Potassium Phosphate, TribasicHCID 68864112Benzyl 3-bromo-6-{[(4-fluorophenyl)sulfonyl]amino}-2-methylbenzoate

生成物 1

HCID 236477655,6-Disubstituted anthranilic acid sulfonamide, 9e

試薬・触媒・溶媒 3

HCID 178479803
HCID 178479803、化合物
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of Example 225A (123 mg, 0.26 mmol), potassium phosphate (192 mg, 0.9 mmol), butylboronic acid (34 mg, 0.33 mmol), bis(tricyclohexylphosphino)palladium dichloride (19 mg, 0.03 mmol), toluene (4 mL), and water (0.2 mL) was purged with argon and shaken at 100° C. for 36 hours in a sealed container. The mixture was diluted with ethyl acetate (10 mL), washed with water (2×10 mL) and brine, dried (Na2SO4), filtered, concentrated and passed through a silica gel cartridge (20 g) with 15% ethyl acetate/hexanes. The isolated solid was substituted for Example 108C in Example 108D and purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min to provide the desired-product. MS (ESI(+)) m/e 383 (M+NH4)+; (ESI(−)) m/e 364 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.09 (br s, 1H), 9.74 (br s, 1H), 7.78 (m, 2H), 7.39 (m, 2H), 7.08 (d, 1H), 6.71 (d, 1H), 2.55 (q, 2H), 2.18 (s, 3H), 1.44 (m, 2H), 1.32 (m, 2H), 0.91 (t, 3H).

後処理

  1. washwashed with water (2×10 mL) and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  6. customover 8 minutes
  7. custom(10 minute run time)
  8. customto provide the desired-product

出典と根拠

ORDレコード
ord-ae1c384e886e4e6883cc58838382736c
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07491718B2

反応ノート

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